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Born in Boston, Massachusetts, Cary spent much of his early life in Boston's Mattapan area (known locally as "Murdapan").[1] Growing up, he forged a friendship with future Gang Starr MC, Guru.[1] The two were separated when Shug was imprisoned and Guru moved to New York, forming Gang Starr with DJ Premier.

On his release, Shug again hooked up with Guru, joined the Gang Starr Foundation, and contributed to each of Gang Starr's albums, beginning with Hard to Earn in 1994 (on "F.A.L.A.").[1] He also appeared on DJ Krush's "Meiso" in 1995 as well as "The Militia" from 1998's Moment of Truth, and contributed to Guru's "Jazzmatazz" albums.[2]

During the 1990s, Shug recorded a few 12-inch singles produced by DJ Premier for Payday and Chrysalis, but his first proper solo album, Who's Hard was not released until 2005 and half of the songs were handled by DJ Premier.[1]

He signed to New York's Babygrande in 2007, and released his second album, Streetchamp.[1] The album was produced by MoSS and DJ Premier and features guest appearances from DJ Premier and Sean Price.[3][4]

A third solo album, Otherside of the Game, was released in November 2008, and features DJ Premier, Bumpy Knuckles, Billy Danze of M.O.P., Termanology, Blaq Poet, and Singapore Kane. He performed at the 2009 Boston hemp fest.[5][6]

He is featured on the single "Tap Out", which appears on M-Dot & DJ Jean Maron's 2010 album Run MPC. The video of "tap out" was directed by Steven TAPIA. In 2010 he also collaborated with (artist) Aztech and (producer) Reel Drama on their album Hybrid Genetics.[7] In 2010 he collaborated with west coast hip hop artist Spinz [8] on a song called "Round Tha World" that was recorded while touring Europe. In 2012 he worked again with Dj Jean Maron for the release of the official remix of "Heavy" a posse cut with M-Dot,Benefit & B.A.M (M.O.P/Lil Fame's cousin).

In 2013 Guy appeared in two movies. In the HBO movie "Clear History," he was door security for the band Chicago. In "The Heat," starring Sandra Bullock and Melissa McCarthy, he was "Tough Guy #2."[9] He also appeared in Boston-based films "The Town", and "Black Mass".

Big Shug released his most recent studio album "Triple OGzus" in March 2015. Shug's upcoming project is entitled "The Living Room Project" according to his Instagram page. As of January 2019, there is no word on the release date of the album. In January 2019, Big Shug announced his new album will be entitled “The Diamond Report” while “The Living Room Project” has been rumored to have been shelved or pushed off but Shug has not confirmed this.

In 2012 and 2014, Big Shug led his Braintree Youth Basketball team to two championships. In 2013, he was defeated in the semi-final which led him to saying "Damn, these kids sign up to hoop, but they can't hoop. They damn bad." This caused an uproar from parents of players in the Braintree Youth Basketball organization. The BYB committee later handed him a two-game suspension which was appealed. After a local court session, the suspension was overturned due to Shug's right to the first amendment. This led to Shug being "pissed off". This made him go into the 2013-14 season on fire. He coached his team led by his son, Trumayne "The Big Dawg" Guy to a second championship in three years. Due to his tremendous season, Shug was awarded "BYB Coach of the Year". In his winning speech, he said "What I said last year was totally disrespectful to all players trying to get better at basketball, a game I love. I'm not apologizing fam' because it was my freedom of speech to say that but I'm happy that I was able to win this year and help make a group of good basketball players, great."